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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (8) Show 8 proteins XML

enzymes (8) Show 8 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-18 08:36:36 UTC

Update Date

2022-03-07 02:49:11 UTC

HMDB ID

HMDB0001925

Secondary Accession Numbers

HMDB0001872
HMDB01872
HMDB01925

Metabolite Identification

Common Name

Ibuprofen

Description

Ibuprofen is a nonsteroidal anti-inflammatory drug (NSAID) widely marketed under various trademarks including Act-3, Advil, Brufen, Motrin, Nuprin, and Nurofen. It is used for relief of symptoms of arthritis, primary dysmenorrhoea, and fever; Ibuprofen is an NSAID which is believed to work through inhibition of cyclooxygenase (COX), thus inhibiting prostaglandin synthesis. There are at least 2 variations of cyclooxygenase (COX-1 and COX-2), ibuprofen inhibits both COX-1 and COX-2. It appears that its analgesic, antipyretic, and anti-inflammatory activity are achieved principally through COX-2 inhibition; whereas COX-1 inhibition is responsible for its unwanted effects on platelet aggregation and the GI mucosa. As with other NSAIDs, ibuprofen inhibits platelet aggregation, but is not used therapeutically for this action since it is a minor and reversible effect. -- Wikipedia .

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0243659
     RDKit          3D
(R)-(-)-Ibuprofen
 33 33  0  0  0  0  0  0  0  0999 V2000
   -4.5860   -0.7797    0.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1556   -0.3158    0.4890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1682    1.2012    0.2699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3408   -0.9264   -0.6278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9097   -0.5345   -0.5496 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0194   -1.2706    0.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3479   -0.9058    0.2298 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8186    0.2230   -0.4073 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2529    0.6252   -0.3352 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1518   -0.4205   -0.9541 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6042    0.9126    1.0612 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7385    0.7983    1.9539 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8700    1.3145    1.4683 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8977    0.9660   -1.1174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4301    0.5950   -1.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1967   -0.6342    1.2142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0259   -0.1403   -0.5085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5639   -1.8084   -0.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7535   -0.5216    1.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3601    1.3629   -0.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9821    1.6841    0.8317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1613    1.5846    0.5575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7278   -0.6023   -1.6029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4275   -2.0393   -0.6088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3489   -2.1666    0.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0766   -1.5033    0.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4018    1.5565   -0.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5787   -0.0859   -1.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5611   -1.3158   -1.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0027   -0.6907   -0.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6872    0.7746    1.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2692    1.8632   -1.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1402    1.1999   -1.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
  8 14  1  0
 14 15  2  0
 15  5  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
M  END

1050
  Mrv1652305271900162D          

 15 15  0  0  1  0            999 V2000
    3.7934    2.7596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    1.5221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -1.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.5221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.0154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -0.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.9346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.9346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  1  0  0  0  0
  2 15  2  0  0  0  0
  3  4  1  0  0  0  0
  3  8  1  0  0  0  0
  3  9  1  0  0  0  0
  4  5  1  0  0  0  0
  5 10  2  0  0  0  0
  5 11  1  0  0  0  0
  6  7  1  0  0  0  0
  6 12  2  0  0  0  0
  6 13  1  0  0  0  0
  7 14  1  0  0  0  0
  7 15  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001925

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CC1=CC=C(C=C1)C(C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H18O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15/h4-7,9-10H,8H2,1-3H3,(H,14,15)

> <INCHI_KEY>
HEFNNWSXXWATRW-UHFFFAOYSA-N

> <FORMULA>
C13H18O2

> <MOLECULAR_WEIGHT>
206.2808

> <EXACT_MASS>
206.13067982

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
23.761548863086013

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[4-(2-methylpropyl)phenyl]propanoic acid

> <ALOGPS_LOGP>
3.50

> <JCHEM_LOGP>
3.8435581993333345

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.851939431757335

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
60.73190000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.84e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ibuprofen, (+-)-

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0243659
     RDKit          3D
(R)-(-)-Ibuprofen
 33 33  0  0  0  0  0  0  0  0999 V2000
   -4.5860   -0.7797    0.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1556   -0.3158    0.4890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1682    1.2012    0.2699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3408   -0.9264   -0.6278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9097   -0.5345   -0.5496 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0194   -1.2706    0.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3479   -0.9058    0.2298 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8186    0.2230   -0.4073 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2529    0.6252   -0.3352 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1518   -0.4205   -0.9541 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6042    0.9126    1.0612 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7385    0.7983    1.9539 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8700    1.3145    1.4683 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8977    0.9660   -1.1174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4301    0.5950   -1.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1967   -0.6342    1.2142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0259   -0.1403   -0.5085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5639   -1.8084   -0.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7535   -0.5216    1.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3601    1.3629   -0.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9821    1.6841    0.8317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1613    1.5846    0.5575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7278   -0.6023   -1.6029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4275   -2.0393   -0.6088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3489   -2.1666    0.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0766   -1.5033    0.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4018    1.5565   -0.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5787   -0.0859   -1.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5611   -1.3158   -1.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0027   -0.6907   -0.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6872    0.7746    1.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2692    1.8632   -1.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1402    1.1999   -1.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
  8 14  1  0
 14 15  2  0
 15  5  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1050                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       7.081   5.151   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       8.415   2.841   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.414  -4.089   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.747  -3.319   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.747  -1.779   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.747   1.301   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.747   2.841   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.414  -5.629   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.080  -3.319   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414  -1.009   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081  -1.009   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414   0.531   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.081   0.531   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414   3.611   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081   3.611   0.000  0.00  0.00           C+0
CONECT    1   15                                                            
CONECT    2   15                                                            
CONECT    3    4    8    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4   10   11                                                  
CONECT    6    7   12   13                                                  
CONECT    7    6   14   15                                                  
CONECT    8    3                                                            
CONECT    9    3                                                            
CONECT   10    5   12                                                       
CONECT   11    5   13                                                       
CONECT   12    6   10                                                       
CONECT   13    6   11                                                       
CONECT   14    7                                                            
CONECT   15    1    2    7                                                  
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0243709
HETATM    1  C1  UNL     1      -4.566   0.503   0.200  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.162  -0.071   0.343  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.127  -1.317  -0.528  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.199   0.936  -0.154  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.793   0.602  -0.115  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.064   0.856   0.940  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.394   0.507   0.901  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.928  -0.118  -0.208  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.369  -0.487  -0.227  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.720  -1.476   0.841  1.00  0.00           C  
HETATM   11  C11 UNL     1       4.218   0.726  -0.168  1.00  0.00           C  
HETATM   12  O1  UNL     1       5.025   0.882   0.782  1.00  0.00           O  
HETATM   13  O2  UNL     1       4.136   1.689  -1.146  1.00  0.00           O  
HETATM   14  C12 UNL     1       1.094  -0.383  -1.275  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.238  -0.026  -1.219  1.00  0.00           C  
HETATM   16  H1  UNL     1      -4.676   1.391   0.871  1.00  0.00           H  
HETATM   17  H2  UNL     1      -4.755   0.875  -0.832  1.00  0.00           H  
HETATM   18  H3  UNL     1      -5.343  -0.253   0.407  1.00  0.00           H  
HETATM   19  H4  UNL     1      -3.055  -0.390   1.371  1.00  0.00           H  
HETATM   20  H5  UNL     1      -4.065  -1.911  -0.422  1.00  0.00           H  
HETATM   21  H6  UNL     1      -2.296  -1.994  -0.225  1.00  0.00           H  
HETATM   22  H7  UNL     1      -3.070  -1.012  -1.589  1.00  0.00           H  
HETATM   23  H8  UNL     1      -2.472   1.201  -1.198  1.00  0.00           H  
HETATM   24  H9  UNL     1      -2.344   1.895   0.426  1.00  0.00           H  
HETATM   25  H10 UNL     1      -0.388   1.345   1.788  1.00  0.00           H  
HETATM   26  H11 UNL     1       2.051   0.712   1.734  1.00  0.00           H  
HETATM   27  H12 UNL     1       3.588  -0.976  -1.209  1.00  0.00           H  
HETATM   28  H13 UNL     1       3.371  -1.159   1.853  1.00  0.00           H  
HETATM   29  H14 UNL     1       4.823  -1.602   0.828  1.00  0.00           H  
HETATM   30  H15 UNL     1       3.269  -2.450   0.552  1.00  0.00           H  
HETATM   31  H16 UNL     1       3.818   2.642  -0.978  1.00  0.00           H  
HETATM   32  H17 UNL     1       1.524  -0.876  -2.146  1.00  0.00           H  
HETATM   33  H18 UNL     1      -0.844  -0.259  -2.086  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    4   19
CONECT    3   20   21   22
CONECT    4    5   23   24
CONECT    5    6    6   15
CONECT    6    7   25
CONECT    7    8    8   26
CONECT    8    9   14
CONECT    9   10   11   27
CONECT   10   28   29   30
CONECT   11   12   12   13
CONECT   13   31
CONECT   14   15   15   32
CONECT   15   33
END

HMDB0243659
     RDKit          3D
(R)-(-)-Ibuprofen
 33 33  0  0  0  0  0  0  0  0999 V2000
   -4.5860   -0.7797    0.3103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1556   -0.3158    0.4890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1682    1.2012    0.2699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3408   -0.9264   -0.6278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9097   -0.5345   -0.5496 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0194   -1.2706    0.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3479   -0.9058    0.2298 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8186    0.2230   -0.4073 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2529    0.6252   -0.3352 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1518   -0.4205   -0.9541 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6042    0.9126    1.0612 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7385    0.7983    1.9539 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8700    1.3145    1.4683 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8977    0.9660   -1.1174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4301    0.5950   -1.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1967   -0.6342    1.2142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0259   -0.1403   -0.5085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5639   -1.8084   -0.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7535   -0.5216    1.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3601    1.3629   -0.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9821    1.6841    0.8317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1613    1.5846    0.5575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7278   -0.6023   -1.6029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4275   -2.0393   -0.6088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3489   -2.1666    0.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0766   -1.5033    0.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4018    1.5565   -0.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5787   -0.0859   -1.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5611   -1.3158   -1.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0027   -0.6907   -0.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6872    0.7746    1.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2692    1.8632   -1.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1402    1.1999   -1.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 11 13  1  0
  8 14  1  0
 14 15  2  0
 15  5  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+-)-2-(p-Isobutylphenyl)propionic acid	ChEBI
(+-)-alpha-Methyl-4-(2-methylpropyl)benzeneacetic acid	ChEBI
(+-)-Ibuprofen	ChEBI
(+-)-p-Isobutylhydratropic acid	ChEBI
(4-Isobutylphenyl)-alpha-methylacetic acid	ChEBI
(RS)-Ibuprofen	ChEBI
2-(4-Isobutylphenyl)propanoic acid	ChEBI
4-Isobutylhydratropic acid	ChEBI
Adran	ChEBI
Advil	ChEBI
alpha-(4-Isobutylphenyl)propionic acid	ChEBI
alpha-(p-Isobutylphenyl)propionic acid	ChEBI
Amibufen	ChEBI
Anco	ChEBI
Anflagen	ChEBI
Apsifen	ChEBI
Bluton	ChEBI
Brufen	ChEBI
Brufort	ChEBI
Buburone	ChEBI
Butylenin	ChEBI
Dolgin	ChEBI
Dolgirid	ChEBI
Dolgit	ChEBI
Dolo-dolgit	ChEBI
Ebufac	ChEBI
Epobron	ChEBI
Femadon	ChEBI
Haltran	ChEBI
Ibu-attritin	ChEBI
Ibumetin	ChEBI
Ibuprocin	ChEBI
Ibutid	ChEBI
Inabrin	ChEBI
Inoven	ChEBI
Lamidon	ChEBI
Lebrufen	ChEBI
Liptan	ChEBI
Medipren	ChEBI
Motrin	ChEBI
Mynosedin	ChEBI
Nobfen	ChEBI
Nobgen	ChEBI
Nuprin	ChEBI
Nurofen	ChEBI
Pediaprofen	ChEBI
Roidenin	ChEBI
Rufen	ChEBI
Seclodin	ChEBI
Suspren	ChEBI
Tabalon	ChEBI
Trendar	ChEBI
Urem	ChEBI
(+-)-2-(p-Isobutylphenyl)propionate	Generator
(+-)-a-Methyl-4-(2-methylpropyl)benzeneacetate	Generator
(+-)-a-Methyl-4-(2-methylpropyl)benzeneacetic acid	Generator
(+-)-alpha-Methyl-4-(2-methylpropyl)benzeneacetate	Generator
(+-)-Α-methyl-4-(2-methylpropyl)benzeneacetate	Generator
(+-)-Α-methyl-4-(2-methylpropyl)benzeneacetic acid	Generator
(+-)-p-Isobutylhydratropate	Generator
(4-Isobutylphenyl)-a-methylacetate	Generator
(4-Isobutylphenyl)-a-methylacetic acid	Generator
(4-Isobutylphenyl)-alpha-methylacetate	Generator
(4-Isobutylphenyl)-α-methylacetate	Generator
(4-Isobutylphenyl)-α-methylacetic acid	Generator
2-(4-Isobutylphenyl)propanoate	Generator
4-Isobutylhydratropate	Generator
a-(4-Isobutylphenyl)propionate	Generator
a-(4-Isobutylphenyl)propionic acid	Generator
alpha-(4-Isobutylphenyl)propionate	Generator
Α-(4-isobutylphenyl)propionate	Generator
Α-(4-isobutylphenyl)propionic acid	Generator
a-(p-Isobutylphenyl)propionate	Generator
a-(p-Isobutylphenyl)propionic acid	Generator
alpha-(p-Isobutylphenyl)propionate	Generator
Α-(p-isobutylphenyl)propionate	Generator
Α-(p-isobutylphenyl)propionic acid	Generator
alpha-p-Isobutylphenylpropionate	HMDB
alpha-p-Isobutylphenylpropionic acid	HMDB
Duralbuprofen	HMDB
p-Isobutyl-2-phenylpropionate	HMDB
p-Isobutyl-2-phenylpropionic acid	HMDB
p-Isobutylhydratropate	HMDB
p-Isobutylhydratropic acid	HMDB
Calcium salt ibuprofen	HMDB
Ibuprofen, copper (2+) salt	HMDB
Ibuprofen, magnesium salt	HMDB
Ibuprofen, zinc salt	HMDB
Trauma dolgit gel	HMDB
Aluminum salt ibuprofen	HMDB
IP 82	HMDB
Ibuprofen, aluminum salt	HMDB
Ibuprofen-zinc	HMDB
Magnesium salt ibuprofen	HMDB
Salt ibuprofen, magnesium	HMDB
Sodium salt ibuprofen	HMDB
Zinc salt ibuprofen	HMDB
I.V. solution, ibuprofen	HMDB
IP-82	HMDB
Ibuprofen i.v. solution	HMDB
Ibuprofen, (+-)-isomer	HMDB
Ibuprofen, (R)-isomer	HMDB
Ibuprofen, (S)-isomer	HMDB
Ibuprofen, calcium salt	HMDB
Potassium salt ibuprofen	HMDB
Salprofen	HMDB
Salt ibuprofen, sodium	HMDB
Salt ibuprofen, zinc	HMDB
alpha-Methyl-4-(2-methylpropyl)benzeneacetic acid	HMDB
Ibuprofen zinc	HMDB
Ibuprofen, potassium salt	HMDB
Ibuprofen, sodium salt	HMDB
Trauma-dolgit gel	HMDB
TraumaDolgit gel	HMDB

Chemical Formula

C₁₃H₁₈O₂

Average Molecular Weight

206.2808

Monoisotopic Molecular Weight

206.13067982

IUPAC Name

2-[4-(2-methylpropyl)phenyl]propanoic acid

Traditional Name

ibuprofen, (+-)-

CAS Registry Number

15687-27-1

SMILES

CC(C)CC1=CC=C(C=C1)C(C)C(O)=O

InChI Identifier

InChI=1S/C13H18O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15/h4-7,9-10H,8H2,1-3H3,(H,14,15)

InChI Key

HEFNNWSXXWATRW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Phenylpropanoic acids

Sub Class

Not Available

Direct Parent

Phenylpropanoic acids

Alternative Parents

Substituents

2-phenylpropanoic-acid
P-cymene
Aromatic monoterpenoid
Monocyclic monoterpenoid
Monoterpenoid
Phenylpropane
Monocyclic benzene moiety
Benzenoid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:5855 )

Ontology

Physiological effect

Adverse health effect

Digestive system disorder

Gastrointestinal disorder

Upper GI Disorder

Eosinophilic esophagitis (PMID: 17334708 , PMID: 32966057 , PMID: 22623390 , +128

Source	Link
Pubmed	PMID: 17334708
Pubmed	PMID: 32966057
Pubmed	PMID: 22623390
Pubmed	PMID: 16870009
Pubmed	PMID: 26910390
Pubmed	PMID: 8087979
Pubmed	PMID: 25105552
Pubmed	PMID: 17349089
Pubmed	PMID: 24023812
Pubmed	PMID: 12376931
Pubmed	PMID: 15992788
Pubmed	PMID: 24341803
Pubmed	PMID: 19468821
Pubmed	PMID: 9625050
Pubmed	PMID: 2420598
Pubmed	PMID: 27012787
Pubmed	PMID: 30830347
Pubmed	PMID: 19551947
Pubmed	PMID: 19309105
Pubmed	PMID: 2026685
Pubmed	PMID: 5727921
Pubmed	PMID: 22024767
Pubmed	PMID: 17031479
Pubmed	PMID: 9439441
Pubmed	PMID: 9625050
Pubmed	PMID: 28649521
Pubmed	PMID: 28649521
Pubmed	PMID: 12097436
Pubmed	PMID: 8257730
Pubmed	PMID: 3168222
Pubmed	PMID: 9869364
Pubmed	PMID: 3436096
Pubmed	PMID: 22157537
Pubmed	PMID: 1246461
Pubmed	PMID: 25691415
Pubmed	PMID: 18004736
Pubmed	PMID: 31506554
Pubmed	PMID: 20423563
Pubmed	PMID: 25536744
Pubmed	PMID: 21388201
Pubmed	PMID: 4903899
Pubmed	PMID: 14708889
Pubmed	PMID: 14967154
Pubmed	PMID: 6774165
Pubmed	PMID: 21389975
Pubmed	PMID: 3709568
Pubmed	PMID: 8311084
Pubmed	PMID: 2242313
Pubmed	PMID: 20549362
Pubmed	PMID: 12555941
Pubmed	PMID: 10731506
Pubmed	PMID: 28157703
Pubmed	PMID: 20576202
Pubmed	PMID: 12368406
Pubmed	PMID: 26066683
Pubmed	PMID: 16736096
Pubmed	PMID: 25597510
Pubmed	PMID: 22800120
Pubmed	PMID: 16139832
Pubmed	PMID: 17287286
Pubmed	PMID: 17301081
Pubmed	PMID: 30817767
Pubmed	PMID: 25851806
Pubmed	PMID: 2587127
Pubmed	PMID: 11893004
Pubmed	PMID: 10102904
Pubmed	PMID: 23430553
Pubmed	PMID: 12705346
Pubmed	PMID: 19075476
Pubmed	PMID: 3571488
Pubmed	PMID: 7776094
Pubmed	PMID: 31963255
Pubmed	PMID: 23093139
Pubmed	PMID: 22284503
Pubmed	PMID: 8503438
Pubmed	PMID: 1246461
Pubmed	PMID: 20502474
Pubmed	PMID: 15558695
Pubmed	PMID: 422265
Pubmed	PMID: 22308371
Pubmed	PMID: 20549362
Pubmed	PMID: 9177981
Pubmed	PMID: 16828325
Pubmed	PMID: 16460720
Pubmed	PMID: 28157703
Pubmed	PMID: 8487492
Pubmed	PMID: 23890588
Pubmed	PMID: 14586528
Pubmed	PMID: 12927681
Pubmed	PMID: 9686366
Pubmed	PMID: 9029640
Pubmed	PMID: 22148915
Pubmed	PMID: 27123458
Pubmed	PMID: 20971021
Pubmed	PMID: 3169394
Pubmed	PMID: 21670092
Pubmed	PMID: 23363473
Pubmed	PMID: 15519880
Pubmed	PMID: 2380628
Pubmed	PMID: 6616873
Pubmed	PMID: 1870421
Pubmed	PMID: 19754154
Pubmed	PMID: 9857238
Pubmed	PMID: 12771321
Pubmed	PMID: 2702744
Pubmed	PMID: 9554495
Pubmed	PMID: 19033659
Pubmed	PMID: 19033659
Pubmed	PMID: 22887155
Pubmed	PMID: 17474139
Pubmed	PMID: 18953024
Pubmed	PMID: 6774165
Pubmed	PMID: 11052553
Pubmed	PMID: 16939360
Pubmed	PMID: 22827565
Pubmed	PMID: 21736852
Pubmed	PMID: 12661026
Pubmed	PMID: 18818040
Pubmed	PMID: 23770102
Pubmed	PMID: 15651030
Pubmed	PMID: 11307586
Pubmed	PMID: 21389975
Pubmed	PMID: 1640293
Pubmed	PMID: 25712379
Pubmed	PMID: 23770102
Pubmed	PMID: 24390407
Pubmed	PMID: 26709303
Pubmed	PMID: 3354621
Pubmed	PMID: 29030856
Pubmed	PMID: 12706375
Pubmed	PMID: 9869358

)

Disposition

Biological location

Cellular substructure

Extracellular

Non-excretory biofluid

Blood

Excreta

Urine

Tissue

Connective tissue

Adipose tissue

Epithelium

Epidermis

Muscle tissue

Skeletal muscle

Organ substructure

Adrenal cortex

Organ

Gland

Adrenal gland

Cell

Neuron

Hematocyte

Platelet

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Ibuprofen action pathway

Metabolic pathway

Ibuprofen metabolism pathway

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	76 °C	Not Available
Boiling Point	319.60 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.021 mg/mL at 25 °C	Not Available
LogP	3.97	AVDEEF,A (1997)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	143.984	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001393

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.068 g/L	ALOGPS
logP	3.5	ALOGPS
logP	3.84	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	4.85	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	60.73 m³·mol⁻¹	ChemAxon
Polarizability	23.76 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	150.267	31661259
DarkChem	[M-H]-	148.484	31661259
AllCCS	[M+H]+	146.587	32859911
AllCCS	[M-H]-	151.555	32859911
DeepCCS	[M+H]+	148.789	30932474
DeepCCS	[M-H]-	145.041	30932474
DeepCCS	[M-2H]-	181.958	30932474
DeepCCS	[M+Na]+	157.501	30932474
AllCCS	[M+H]+	146.6	32859911
AllCCS	[M+H-H2O]+	142.5	32859911
AllCCS	[M+NH4]+	150.3	32859911
AllCCS	[M+Na]+	151.4	32859911
AllCCS	[M-H]-	151.6	32859911
AllCCS	[M+Na-2H]-	152.2	32859911
AllCCS	[M+HCOO]-	153.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Ibuprofen	CC(C)CC1=CC=C(C=C1)C(C)C(O)=O	2622.1	Standard polar	33892256
Ibuprofen	CC(C)CC1=CC=C(C=C1)C(C)C(O)=O	1591.8	Standard non polar	33892256
Ibuprofen	CC(C)CC1=CC=C(C=C1)C(C)C(O)=O	1633.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ibuprofen,1TMS,isomer #1	CC(C)CC1=CC=C(C(C)C(=O)O[Si](C)(C)C)C=C1	1614.9	Semi standard non polar	33892256
Ibuprofen,1TBDMS,isomer #1	CC(C)CC1=CC=C(C(C)C(=O)O[Si](C)(C)C(C)(C)C)C=C1	1858.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Ibuprofen GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-02t9-1910000000-23f448d7be7d5cc35682	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ibuprofen GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-02t9-1910000000-cbe52d63986b68a2cec0	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ibuprofen GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-00di-9300000000-cc259b7768023e4cdba8	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ibuprofen EI-B (Non-derivatized)	splash10-03di-3910000000-618880f8fd7b8ec3d473	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ibuprofen GC-EI-TOF (Non-derivatized)	splash10-02t9-1910000000-23f448d7be7d5cc35682	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ibuprofen GC-EI-TOF (Non-derivatized)	splash10-02t9-1910000000-cbe52d63986b68a2cec0	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Ibuprofen GC-EI-TOF (Non-derivatized)	splash10-00di-9300000000-cc259b7768023e4cdba8	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ibuprofen GC-MS (Non-derivatized) - 70eV, Positive	splash10-0296-3900000000-497aad6d6a3e7af1ac0a	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ibuprofen GC-MS (1 TMS) - 70eV, Positive	splash10-0309-8940000000-13dc492b216fb21dde05	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ibuprofen GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ibuprofen GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ibuprofen GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03xr-3900000000-e20ef3c30496e17720ba	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ibuprofen Quattro_QQQ 10V, N/A-QTOF (Annotated)	splash10-03di-0910000000-90bf6813134491c9fbfd	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ibuprofen Quattro_QQQ 25V, N/A-QTOF (Annotated)	splash10-001i-9800000000-56f599abc462380b648c	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ibuprofen EI-B (HITACHI RMU-6E) , Positive-QTOF	splash10-03di-3910000000-618880f8fd7b8ec3d473	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ibuprofen LC-ESI-qTof , Positive-QTOF	splash10-0006-0497000000-fa397d6ffd29da116900	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ibuprofen LC-ESI-qTof , Positive-QTOF	splash10-0a4i-0690000000-f598b8bee69a6b62e817	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ibuprofen , positive-QTOF	splash10-03di-1900000000-f1b7a986fee133d97eb1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ibuprofen , positive-QTOF	splash10-03di-0920000000-aa36b3244e32560bb9d5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ibuprofen 10V, Negative-QTOF	splash10-03di-0900000000-5542c131f02b637029d8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ibuprofen 40V, Negative-QTOF	splash10-03di-9200000000-5de1fac09e33bce1cc34	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ibuprofen 30V, Negative-QTOF	splash10-0a4i-0900000000-c254195738a6348894be	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ibuprofen 10V, Negative-QTOF	splash10-0a4i-0900000000-d4b4b28d0bf1144854c3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ibuprofen 15V, Negative-QTOF	splash10-0a4i-0900000000-5f5841ab0d19d92f329f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Ibuprofen 20V, Negative-QTOF	splash10-03dl-7900000000-811cee3d7fc26d62724a	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ibuprofen 10V, Positive-QTOF	splash10-0a4i-1970000000-50ac0f9eaf22b22ff57f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ibuprofen 20V, Positive-QTOF	splash10-0bti-2910000000-a5804838ebd627fea205	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ibuprofen 40V, Positive-QTOF	splash10-0pb9-4900000000-a5b30d0a96d30db5ea4a	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ibuprofen 10V, Negative-QTOF	splash10-0a4i-0490000000-27a27175d7bf2807ff33	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ibuprofen 20V, Negative-QTOF	splash10-08fr-1940000000-f33172b037148de8a091	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ibuprofen 40V, Negative-QTOF	splash10-02ha-5900000000-ebc408aaffe3ab58a6a3	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ibuprofen 10V, Positive-QTOF	splash10-0bti-0930000000-d13739453cc1a7af3307	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ibuprofen 20V, Positive-QTOF	splash10-0bud-2910000000-db9b1bc4f7d1e33abb3c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ibuprofen 40V, Positive-QTOF	splash10-0006-9510000000-6eaaec80d704e4b4603c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ibuprofen 10V, Negative-QTOF	splash10-0a4i-0090000000-5535f56d1e770e37902d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ibuprofen 20V, Negative-QTOF	splash10-08fr-0900000000-1aedbd14d6db0c13aa63	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ibuprofen 40V, Negative-QTOF	splash10-014i-0900000000-9537810cacf26548c24a	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	2012-12-05	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Urine

Tissue Locations

Adipose Tissue
Adrenal Cortex
Adrenal Gland
Bladder
Epidermis
Fibroblasts
Intestine
Kidney
Neuron
Pancreas
Placenta
Platelet
Prostate
Skeletal Muscle
Spleen
Testis

Pathways

Name	SMPDB/PathBank	KEGG
Ibuprofen Action Pathway		Not Available
Ibuprofen Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	242.0 (2.42-485.0) uM	Adult (>18 years old)	Both	Normal	8496270	details
Urine	Detected and Quantified	6.513 +/- 6.212 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Cerebrospinal Fluid (CSF)	Detected and Quantified	1.528 +/- 0.563 uM	Adult (>18 years old)	Both	nerve root compression pain	8527289	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.815 +/- 0.296 uM	Adult (>18 years old)	Both	nerve root compression pain	8527289	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.000592 +/- 0.000170 uM	Adult (>18 years old)	Both	Bronchial carcinoma	15078741	details
Urine	Detected and Quantified	3.408 +/- 2.229 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

DB01050

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022743

KNApSAcK ID

Not Available

Chemspider ID

3544

KEGG Compound ID

C01588

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ibuprofen

METLIN ID

572

PubChem Compound

3672

PDB ID

Not Available

ChEBI ID

5855

Food Biomarker Ontology

Not Available

VMH ID

IBUP_R

MarkerDB ID

Not Available

Good Scents ID

rw1204091

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Perioli L, Ambrogi V, Angelici F, Ricci M, Giovagnoli S, Capuccella M, Rossi C: Development of mucoadhesive patches for buccal administration of ibuprofen. J Control Release. 2004 Sep 14;99(1):73-82. [PubMed:15342182 ]
Whitlam JB, Brown KF, Crooks MJ, Room GF: Transsynovial distribution of ibuprofen in arthritic patients. Clin Pharmacol Ther. 1981 Apr;29(4):487-92. [PubMed:7471614 ]
Al-Saidan SM: Transdermal self-permeation enhancement of ibuprofen. J Control Release. 2004 Nov 24;100(2):199-209. [PubMed:15544868 ]
Albert KS, Gernaat CM: Pharmacokinetics of ibuprofen. Am J Med. 1984 Jul 13;77(1A):40-6. [PubMed:6465162 ]
Alam I, Ferrell LD, Bass NM: Vanishing bile duct syndrome temporally associated with ibuprofen use. Am J Gastroenterol. 1996 Aug;91(8):1626-30. [PubMed:8759674 ]
Townsend RJ, Benedetti TJ, Erickson SH, Cengiz C, Gillespie WR, Gschwend J, Albert KS: Excretion of ibuprofen into breast milk. Am J Obstet Gynecol. 1984 May 15;149(2):184-6. [PubMed:6720796 ]
Horn AC, Jarrett SW: Ibuprofen-induced aseptic meningitis in rheumatoid arthritis. Ann Pharmacother. 1997 Sep;31(9):1009-11. [PubMed:9296242 ]
Van Overmeire B, Allegaert K, Casaer A, Debauche C, Decaluwe W, Jespers A, Weyler J, Harrewijn I, Langhendries JP: Prophylactic ibuprofen in premature infants: a multicentre, randomised, double-blind, placebo-controlled trial. Lancet. 2004 Nov 27-Dec 3;364(9449):1945-9. [PubMed:15567010 ]
Castillo M, Smith PC: Disposition and reactivity of ibuprofen and ibufenac acyl glucuronides in vivo in the rhesus monkey and in vitro with human serum albumin. Drug Metab Dispos. 1995 May;23(5):566-72. [PubMed:7587932 ]
Hockertz S, Heckenberger R, Emmendorffer A, Muller M: Influence of ibuprofen on the infection with Listeria monocytogenes. Arzneimittelforschung. 1995 Jan;45(1):104-7. [PubMed:7893261 ]
Day RO, Williams KM, Graham GG, Lee EJ, Knihinicki RD, Champion GD: Stereoselective disposition of ibuprofen enantiomers in synovial fluid. Clin Pharmacol Ther. 1988 May;43(5):480-7. [PubMed:3365913 ]
Trappe TA, White F, Lambert CP, Cesar D, Hellerstein M, Evans WJ: Effect of ibuprofen and acetaminophen on postexercise muscle protein synthesis. Am J Physiol Endocrinol Metab. 2002 Mar;282(3):E551-6. [PubMed:11832356 ]
Laffi G, Daskalopoulos G, Kronborg I, Hsueh W, Gentilini P, Zipser RD: Effects of sulindac and ibuprofen in patients with cirrhosis and ascites. An explanation for the renal-sparing effect of sulindac. Gastroenterology. 1986 Jan;90(1):182-7. [PubMed:3079594 ]
Goldenberg NA, Jacobson L, Manco-Johnson MJ: Brief communication: duration of platelet dysfunction after a 7-day course of Ibuprofen. Ann Intern Med. 2005 Apr 5;142(7):506-9. [PubMed:15809462 ]
Yao M, Zhou W, Sangha S, Albert A, Chang AJ, Liu TC, Wolfe MM: Effects of nonselective cyclooxygenase inhibition with low-dose ibuprofen on tumor growth, angiogenesis, metastasis, and survival in a mouse model of colorectal cancer. Clin Cancer Res. 2005 Feb 15;11(4):1618-28. [PubMed:15746067 ]
Jabor VA, Lanchote VL, Bonato PS: Enantioselective analysis of ibuprofen in human plasma by anionic cyclodextrin-modified electrokinetic chromatography. Electrophoresis. 2002 Sep;23(17):3041-7. [PubMed:12207314 ]
Salas-Herrera IG, Pearson RM, Turner P: Concentration of ibuprofen in cervical mucus. J Pharm Pharmacol. 1991 Feb;43(2):142-4. [PubMed:1672904 ]

Enzymes

Enzyme Details

1. Amine oxidase [flavin-containing] B

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:: MAOB
Uniprot ID:: P27338
Molecular weight:: 58762.475

Enzyme Details

2. Aldo-keto reductase family 1 member C1

General function:: Involved in oxidoreductase activity
Specific function:: Converts progesterone to its inactive form, 20-alpha-dihydroxyprogesterone (20-alpha-OHP). In the liver and intestine, may have a role in the transport of bile. May have a role in monitoring the intrahepatic bile acid concentration. Has a low bile-binding ability. May play a role in myelin formation.
Gene Name:: AKR1C1
Uniprot ID:: Q04828
Molecular weight:: 36788.02

Enzyme Details

3. Aldo-keto reductase family 1 member C2

General function:: Involved in oxidoreductase activity
Specific function:: Works in concert with the 5-alpha/5-beta-steroid reductases to convert steroid hormones into the 3-alpha/5-alpha and 3-alpha/5-beta-tetrahydrosteroids. Catalyzes the inactivation of the most potent androgen 5-alpha-dihydrotestosterone (5-alpha-DHT) to 5-alpha-androstane-3-alpha,17-beta-diol (3-alpha-diol). Has a high bile-binding ability.
Gene Name:: AKR1C2
Uniprot ID:: P52895
Molecular weight:: 15747.91

Enzyme Details

4. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Ibuprofen → 3,4,5-trihydroxy-6-({2-[4-(2-methylpropyl)phenyl]propanoyl}oxy)oxane-2-carboxylic acid	details

Enzyme Details

5. Prostaglandin G/H synthase 2

General function:: Involved in peroxidase activity
Specific function:: Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:: PTGS2
Uniprot ID:: P35354
Molecular weight:: 68995.625

Enzyme Details

6. Prostaglandin G/H synthase 1

General function:: Involved in peroxidase activity
Specific function:: May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:: PTGS1
Uniprot ID:: P23219
Molecular weight:: 68685.82

Enzyme Details

7. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

Enzyme Details

8. Serum albumin

General function:: Involved in transport
Specific function:: Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc
Gene Name:: ALB
Uniprot ID:: P02768
Molecular weight:: 69365.9

Showing metabocard for Ibuprofen (HMDB0001925)

MOL for HMDB0001925 (Ibuprofen)

3D MOL for HMDB0001925 (Ibuprofen)

3D SDF for HMDB0001925 (Ibuprofen)

3D-SDF for HMDB0001925 (Ibuprofen)

PDB for HMDB0001925 (Ibuprofen)

3D PDB for HMDB0001925 (Ibuprofen)

SMILES for HMDB0001925 (Ibuprofen)

INCHI for HMDB0001925 (Ibuprofen)

Structure for HMDB0001925 (Ibuprofen)

3D Structure for HMDB0001925 (Ibuprofen)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions